Chapter 14 – The Synthesis of Seven-Membered Rings in Natural Products

Abstract Seven-membered all carbon atom rings are relatively uncommon structural units found in natural products, especially terpenoids and alkaloids. The total synthesis of these relevant bioactive molecules frequently involves a six-membered ring undergoing a one-carbon atom ring expansion as an important transformation. In this review, we describe recent methodologies for effecting such synthetic sequences, within the context of total syntheses. The use of readily available monoterpene chirons is emphasized for their obvious synthetic advantages.